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Acetic Anhydride → 4-Acetyl-3-(4-fluorophenyl)-2-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

HRID 2260536
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2260536
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH2:16][CH2:15][CH2:14][NH:13][C:12]=23)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>ClCCCl>[C:30]([N:13]1[CH2:14][CH2:15][CH2:16][N:11]2[N:10]=[C:9]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:12]12)(=[O:32])[CH3:31]
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Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 136087720HCID 136087720, Verbindung

Produkt 1

HCID 199572914-Acetyl-3-(4-fluorophenyl)-2-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-fluorophenyl)-2-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (100 mg), triethylamine (0.4 ml) and acetic anhydride (0.2 ml) in dry 1,2-dichloroethane (3 ml) was refluxed for 2 days. The reaction mixture was cooled and concentrated in vacuo. The residue was dissolved in dichloromethane and the solution was washed with an aqueous saturated sodium bicarbonate solution and brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from diisopropyl ether to give 4-acetyl-3-(4-fluorophenyl)-2-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (60 mg).

Aufarbeitung

  1. temperaturewas refluxed for 2 days
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washthe solution was washed with an aqueous saturated sodium bicarbonate solution and brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel
  9. customthe obtained oil was crystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8b1ad3800ef3401fa92ee37d0e081bba
Quelldatensatz
uspto-grants-1995_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05478827

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